Certain 1-carbothioamides of 1,8-naphthyridines, pyrrolo(2,3-b)pyridines and pyrido(2,3-b)azepines

Abstract

The invention relates to thioureas which are derivatives of organic nitrogen compounds containing a pyridine ring to which is fused a saturated nitrogen containing ring which carries on its nitrogen atom a thioamide or substituted thioamide group. The compounds are anti-ulcer agents or intermediates therefor.

I claim: 
     
       1. A compound of formula (I) ##SPC5## or a pharmaceutically acceptable acid addition salt thereof wherein R 1 , R 2  and R 3  are the same or different and represent a hydrogen atom or a lower alkyl, phenyl lower alkyl or, phenyl radical, any of which radicals may be substituted by lower alkyl, lower alkoxy, halogen, nitro or trifluoromethyl, Q is the group ##EQU2## wherein N of said group is directly attached to the alpha carbon of pyridine ring, m is 1, 2 or 3, and the group Q may be substituted by lower alkyl, phenyl lower alkyl, or phenyl radicals any of which radicals may be substituted by lower alkyl, lower alkoxy, halogen, nitro or trifluoromethyl and R 4  is hydrogen or alkyl of 1-3 carbon atoms.   
     
     
       2. A compound as claimed in claim 1, wherein R 1 , R 2  and R 3  are selected from hydrogen and methyl. 
     
     
       3. A compound as claimed in claim 1, wherein R 4  is methyl. 
     
     
       4. A compound as claimed in claim 1, which has formula (Ia) ##SPC6## wherein R 1 , R 2 , R 3 , R 4  and m are as defined in claim 1.   
     
     
       5. A compound as claimed in claim 1 which has formula II. ##SPC7## or a pharmaceutically acceptable acid addition salt thereof wherein R 1 , R 2  and R 3  are as defined in claim 1 and R 5  is hydrogen or methyl.   
     
     
       6. A compound as claimed in claim 1, which is 6,7,8,9-Tetrahydro-9-(N-methylthiocarboxamido)-5H-pyrido[2,3-b] azepine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       7. A compound as claimed in claim 1, which is 1,2,3,4-tetrahydro-1-(N-methylthiocarboxamido)-1,8-naphthyridine. 
     
     
       8. A compound as claimed in claim 1 which is 2,3-dihydro-N-methyl-1H-pyrrolo[2,3-b]pyridine-1-carbothioamide. 
     
     
       9. A compound as claimed in claim 1 which is 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carbothioamide.